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Chemistry

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Also known as: Eltanolone, 128-20-1, 3alpha-hydroxy-5beta-pregnan-20-one, Pregnan-3alpha-ol-20-one, Pregnanolone ii, Eltanolona

Molecular Formula

C₂₁H₃₄O₂

Molecular Weight

318.5 g/mol

InChI Key

AURFZBICLPNKBZ-YZRLXODZSA-N

FDA UNII

BXO86P3XXW

A pregnane found in the urine of pregnant women and sows. It has anesthetic, hypnotic, and sedative properties.

1 2D Structure

Allopregnanolone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(3R,5R,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

2.1.2 InChI

InChI=1S/C21H34O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h14-19,23H,4-12H2,1-3H3/t14-,15-,16+,17-,18+,19+,20+,21-/m1/s1

2.1.3 InChI Key

AURFZBICLPNKBZ-YZRLXODZSA-N

2.1.4 Canonical SMILES

CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C

2.1.5 Isomeric SMILES

CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)C

2.2 Other Identifiers

2.2.1 UNII

BXO86P3XXW

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3 Alpha Hydroxy 5 Alpha Pregnan 20 One

2. 3 Alpha Hydroxy 5 Beta Pregnan 20 One

3. 3 Alpha, 5 Beta Tetrahydroprogesterone

4. 3 Alpha, 5 Beta-tetrahydroprogesterone

5. 3 Alpha-hydroxy-5 Alpha-pregnan-20-one

6. 3 Alpha-hydroxy-5 Beta-pregnan-20-one

7. 3 Hydroxypregnan 20 One

8. 3-hydroxypregnan-20-one

9. 3beta Hydroxy 5alpha Pregnan 20 One

10. 3beta-hydroxy-5alpha-pregnan-20-one

11. Allopregnan 3 Beta Ol 20 One

12. Allopregnan-3 Beta-ol-20-one

13. Allopregnanolone

14. Alpha-hydroxy-5 Alpha-pregnan-20-one, 3

15. Alpha-hydroxy-5 Beta-pregnan-20-one, 3

16. Alpha-pregnan-20-one, 3 Alpha-hydroxy-5

17. Beta-ol-20-one, Allopregnan-3

18. Beta-pregnan-20-one, 3 Alpha-hydroxy-5

19. Eltanolone

20. Epipregnanolone

21. Pregnan 3alpha Ol 20 One

22. Pregnan-3alpha-ol-20-one

23. Pregnanolone, (3alpha)-isomer

24. Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer

25. Pregnanolone, (3alpha,5alpha)-isomer

26. Pregnanolone, (3alpha,5beta)-isomer

27. Pregnanolone, (3beta)-isomer

28. Pregnanolone, (3beta, 5alpha)-isomer

29. Pregnanolone, (3beta, 5alpha, 17alpha)-isomer

30. Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer

31. Pregnanolone, (3beta, 5beta)-isomer

32. Pregnanolone, (3beta, 5beta, 17alpha)-isomer

33. Pregnanolone, (3beta, 5beta,14beta)-isomer

34. Pregnanolone, (5alpha)-isomer

35. Sepranolone

2.3.2 Depositor-Supplied Synonyms

1. Eltanolone

2. 128-20-1

3. 3alpha-hydroxy-5beta-pregnan-20-one

4. Pregnan-3alpha-ol-20-one

5. Pregnanolone Ii

6. Eltanolona

7. Eltanolonum

8. Eltanolone [inn]

9. Skf 6455

10. Allopregnanolone

11. Nsc 82867

12. 5beta-pregnan-3alpha-ol-20-one

13. (3alpha,5beta)-3-hydroxypregnan-20-one

14. Kabi 2213

15. Kabi-2213

16. 3alpha-hydroxy-5beta-pregnane-20-one

17. Pregnan-20-one, 3-hydroxy-, (3alpha,5beta)-

18. Pregnan-3.alpha.-ol-20-one

19. Nsc-82867

20. Bxo86p3xxw

21. 3.alpha.-hydroxy-5.beta.-pregnan-20-one

22. Chebi:1712

23. 5.beta.-pregnan-20-one, 3.alpha.-hydroxy-

24. Skf-6455

25. 1-[(3r,5r,8r,9s,10s,13s,14s,17s)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]ethanone

26. 3.alpha.,5.beta.-epimeric Pregnanolone

27. 3.alpha.-hydroxy-5.beta.-tetrahydroprogesterone

28. Pregnan-20-one, 3-hydroxy-, (3.alpha.,5.beta.)-

29. Eltanolonum [inn-latin]

30. Eltanolona [inn-spanish]

31. 1-((3r,5r,8r,9s,10s,13s,14s,17s)-3-hydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethan-1-one

32. Allopregnan-3 Beta-ol-20-one

33. 3alpha-hydroxy-5beta-tetrahydroprogesterone

34. 3alpha,5beta-epimeric Pregnanolone

35. Pregnan-3a-ol-20-one

36. Mls002694512

37. Unii-bxo86p3xxw

38. Pregnanolone, (3alpha,5beta)-isomer

39. 3 Hydroxypregnan 20 One

40. Pregnan 3alpha Ol 20 One

41. 3 Alpha, 5 Beta-tetrahydroprogesterone

42. Brn 4785659

43. 3 Alpha-hydroxy-5 Beta-pregnan-20-one

44. 3-alpha-hydroxy-5-beta-pregnan-20-one

45. 3 Alpha-hydroxy-5 Alpha-pregnan-20-one

46. Pregnanolone, (3beta)-isomer

47. Pregnanolone, (3alpha)-isomer

48. Pregnanolone, (5alpha)-isomer

49. Allopregnan 3 Beta Ol 20 One

50. Beta-ol-20-one, Allopregnan-3

51. (3?,5?)-3-hydroxy-pregnan-20-one

52. 3alpha,5beta-thp

53. 3beta Hydroxy 5alpha Pregnan 20 One

54. Pregnanolone, (3alpha,5alpha)-isomer

55. Pregnanolone, (3beta, 5beta)-isomer

56. Pregnanolone, (3beta, 5alpha)-isomer

57. 3 Alpha, 5 Beta Tetrahydroprogesterone

58. Wln: L E5 B666tj A1 E1 Fv1 Oq

59. 3 Alpha Hydroxy 5 Beta Pregnan 20 One

60. 5beta-pregnan-20-one, 3alpha-hydroxy-

61. 3 Alpha Hydroxy 5 Alpha Pregnan 20 One

62. Alpha-hydroxy-5 Beta-pregnan-20-one, 3

63. Beta-pregnan-20-one, 3 Alpha-hydroxy-5

64. 5-beta-pregnan-20-one, 3-alpha-hydroxy-

65. Alpha-hydroxy-5 Alpha-pregnan-20-one, 3

66. Alpha-pregnan-20-one, 3 Alpha-hydroxy-5

67. Kabi2213

68. Pregnan-20-one, 3-hydroxy-, (3a,5b)-

69. Pregnanolone, (3beta, 5beta,14beta)-isomer

70. Pregnanolone, (3beta, 5beta, 17alpha)-isomer

71. Eltanolone [mart.]

72. Pregnanolone, (3beta, 5alpha, 17alpha)-isomer

73. Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer

74. Schembl56664

75. 3-hydroxy-5-pregnan-20-one

76. 5?-pregnan-3?-ol-20-one

77. Chembl210952

78. 3.alpha.,5.beta.-pregnanolone

79. 3a-hydroxy-5b-pregnan-20-one

80. Dtxsid1046342

81. Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer

82. Gtpl11534

83. Skf6455

84. 3alpha,5beta-tetrahydroprogesterone

85. Nsc82867

86. Zinc3800039

87. (3a,5b)-3-hydroxypregnan-20-one

88. Lmst02030175

89. Db12308

90. 5 Beta -pregnan-3 Alpha -ol-20-one

91. 5.beta.-pregnan-3.alpha.-ol-20-one

92. Pregnan-20-one, (3.alpha.,5.beta.)-

93. (3alpha,5beta)-3-hydroxy-pregnan-20-one

94. Pregnan-3.alpha.-ol-20-one [mi]

95. B7455

96. C05480

97. 128p201

98. 3-hydroxypregnan-20-one, (3.alpha.,5.beta.)-

99. J-005571

100. Q18344323

101. 1-((3r,5r,8r,9s,10s,13s,14s,17s)-3-hydroxy-10,13-dimethylhexadecahydro-1h-cyclopenta[a]phenanthren-17-yl)ethanone

102. 110350-90-8

103. P9n

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₃₄O₂
Molecular Weight	318.5 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	318.255880323 g/mol
Monoisotopic Mass	318.255880323 g/mol
Topological Polar Surface Area	37.3 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	500
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment of postpartum depression

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anesthetics

Agents capable of inducing a total or partial loss of sensation, especially tactile sensation and pain. They may act to induce general ANESTHESIA, in which an unconscious state is achieved, or may act locally to induce numbness or lack of sensation at a targeted site. (See all compounds classified as Anesthetics.)

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